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Nucleophilic substitution sulfonation in emulsions: Formation of sodium benzyl sulfonate
Author(s) -
Husein Maen M.,
Weber Martin E.,
Vera Juan H.
Publication year - 2001
Publication title -
the canadian journal of chemical engineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.404
H-Index - 67
eISSN - 1939-019X
pISSN - 0008-4034
DOI - 10.1002/cjce.5450790507
Subject(s) - chemistry , bromide , pulmonary surfactant , benzyl chloride , chloride , counterion , sulfonate , sodium , nucleophilic substitution , emulsion , cationic polymerization , inorganic chemistry , medicinal chemistry , sodium bromide , benzyl bromide , nucleophile , reaction rate , saturation (graph theory) , polymer chemistry , organic chemistry , catalysis , ion , biochemistry , mathematics , combinatorics
Benzyl bromide was sulfonated at 298 K in emulsions formed with dioctyldimethylammonium bromide, or chloride. If mixing was sufficient, the emulsion was maintained throughout the reaction period. Lower conversions were obtained whenever benzyl bromide phase separated from the mixture. Chloride as surfactant counterion gave higher reaction rate, but decreased the conversion to C 7 H 7 SO 3 − Na + due to formation of benzyl chloride. The conversion to C 7 H 7 SO 3 − Na + displayed a broad maximum as R 2 (Me) 2 − N + Br concentration increased. Except at low concentration, the reaction rate increased with the concentration of Na 2 SO 3 in accord with the S N 2 mechanism. The reaction rate increased with the reactant concentrations until interface saturation was achieved, suggesting that product formation did not interfere with the access of the reactants to the interface.